PROBLEM: Recently while building it myself I found an interesting but/feature of chrome. When I was debugging my 301 redirect handler the first time I hit the URL it hit my breakpoint and I could debug the update however when I hit it again it redirected without hitting my handler. It turns out this is a feature of chrome. Since the 301 is a permanent redirect, Chrome remembers the redirect and caches it.
Here is an article that explains it more: Google Chrome Caches 301 Redirects

SOLUTION: There are actually two possible solutions:

Debug in Internet Explorer and FireFox and once working use Chrome once to ensure it redirects.